[Retroman1969]

Congrats, it's a great version of the Boxster and one worth restoring.
Honestly, I've seen many high mileage and dogged out 986s before but I've never seen peeling paint or clear coat on one before. I'd almost guarantee that there has been some damage repair on that car. The seat looks like it has been severely water damaged at some point judging by the pattern of disintegration of the leather. (Also notice the wrinkling-shrinkage around the edges)
The top issue could easily be the micro switch in the parking brake handle. It's a very common failure, and it will act like the whole system is dead. (But the parking brake light will still come on like normal).
I can say fairly confidently that you are going to have the same or more invested in this car as the price of a low mileage super clean example before it's over, but you will have the confidence that every possible issue has been addressed and that it will be solid car at that point.